3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

Base Information

Chemical Name:3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide
CAS No.:459170-46-8
Molecular Formula:C₁₈H₁₉BrF₃NO₆Se
Molecular Weight:561.211
Hs Code.:

Synonyms:3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

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Chemical Property of 3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

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Technology Process of 3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

There total 8 articles about 3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 459170-45-7
p-methoxyphenyl 3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-β-D-glucopyranoside

: 459170-46-8
3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

Guidance literature:: With Acetyl bromide; boron trifluoride diethyl etherate; zinc(II) iodide; In chloroform; at 0 - 40 ℃; for 16.5h;
DOI:10.1021/ja0127234

Reference yield:

: 138906-43-1
4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 459170-46-8
3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / NBS; BaCO₃ / CCl₄ / 1 h / Heating

2: 61 percent / i-Pr₂NEt / tetrahydrofuran / 27 h / Heating

3: 91 percent / Et₃N / tetrahydrofuran / 24 h / Heating

4: 96 percent / N₂H₄*H₂O / ethanol / 17 h / 95 - 110 °C

5: pyridine / 0.5 h

6: 1.18 g / pyridine / 20 °C

7: 88 percent / BF₃*Et₂O / CHCl₃ / 7 h

8: AcBr; BF₃*Et₂O; ZnI₂ / CHCl₃ / 16.5 h / 0 - 40 °C

With pyridine; N-Bromosuccinimide; Acetyl bromide; boron trifluoride diethyl etherate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; barium carbonate; zinc(II) iodide; In tetrahydrofuran; tetrachloromethane; ethanol; chloroform;
DOI:10.1021/ja0127234

Reference yield:

: 459170-41-3
p-methoxyphenyl 3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-phenylseleno-2-amino-β-D-glucopyranoside

: 459170-46-8
3,4-di-O-acetyl-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-α-D-glucopyranosyl bromide

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 0.5 h

2: 1.18 g / pyridine / 20 °C

3: 88 percent / BF₃*Et₂O / CHCl₃ / 7 h

4: AcBr; BF₃*Et₂O; ZnI₂ / CHCl₃ / 16.5 h / 0 - 40 °C

With pyridine; Acetyl bromide; boron trifluoride diethyl etherate; zinc(II) iodide; In chloroform;
DOI:10.1021/ja0127234